EP1608612A1 - Process for producing cyclohexenone long-chain alcohols - Google Patents
Process for producing cyclohexenone long-chain alcoholsInfo
- Publication number
- EP1608612A1 EP1608612A1 EP03715611A EP03715611A EP1608612A1 EP 1608612 A1 EP1608612 A1 EP 1608612A1 EP 03715611 A EP03715611 A EP 03715611A EP 03715611 A EP03715611 A EP 03715611A EP 1608612 A1 EP1608612 A1 EP 1608612A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- mmol
- cyclohexen
- methyl
- cyclohexenone long
- chain alcohol
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/587—Unsaturated compounds containing a keto groups being part of a ring
- C07C49/753—Unsaturated compounds containing a keto groups being part of a ring containing ether groups, groups, groups, or groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/51—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition
- C07C45/511—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition involving transformation of singly bound oxygen functional groups to >C = O groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/51—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition
- C07C45/511—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition involving transformation of singly bound oxygen functional groups to >C = O groups
- C07C45/513—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition involving transformation of singly bound oxygen functional groups to >C = O groups the singly bound functional group being an etherified hydroxyl group
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
- C07C45/68—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
- C07C45/68—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
- C07C45/70—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction with functional groups containing oxygen only in singly bound form
- C07C45/71—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction with functional groups containing oxygen only in singly bound form being hydroxy groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/587—Unsaturated compounds containing a keto groups being part of a ring
- C07C49/703—Unsaturated compounds containing a keto groups being part of a ring containing hydroxy groups
- C07C49/713—Unsaturated compounds containing a keto groups being part of a ring containing hydroxy groups a keto group being part of a six-membered ring
Definitions
- the present invention relates to a process for producing a cyclohexenone long-chain alcohol, which process requires a reduced number of reaction steps and can be performed with ease and is thus industrially advantageous.
- Nerve growth factor which is found in particular abundance in the hippocampus and cerebral cortex of the brain, is a neurotrophic factor which is required by a living body for sustaining life and functions and stimulates differentiation and growth of neurons.
- NGF acts on cholinergic neurons. Alzheimer's disease is accepted to exhibit a primary lesion of regeneration and falling of cholinergic neurons, and on the basis of this understanding, NGF has been administered to the brain as therapy for the disease.
- NGF being a protein having a molecular weight of 12,000, cannot pass through the blood-brain barrier, and thus does not serve as practical means for the treatment of Alzheimer's disease.
- cyclohexenone long-chain alcohol has a low molecular weight and is known to be useful as a prophylactic or therapeutic drug for cerebral diseases such as dementia, in view that, when administered orally, the alcohol reaches the brain, passes through the blood-brain barrier, and at low concentration exhibits excellent effect to stimulate growth of neurons, to thereby directly act on neurites to elicit extension (Japanese Kohyo (PCT) Patent Publication No. 2U01- 515058) .
- cyclohexenone long-chain alcohol has been produced through a complicated process; for example, by reacting cyclohexanone or methyl-substituted 2-cyclohexen-l- one with benzenesulfinate in the presence of acid, then with ethylene glycol to form a ketal compound, and further with ⁇ -halogenoalcanol, followed by treatment with an acid to remove a protective group.
- cyclohexanone or methyl-substituted 2-cyclohexen-l- one with benzenesulfinate in the presence of acid, then with ethylene glycol to form a ketal compound, and further with ⁇ -halogenoalcanol, followed by treatment with an acid to remove a protective group.
- 3- (14-hydroxytetradecyl) -4-methyl-2-cyclohexen- 1-one from a starting material 3-methylcyclohexenone
- seven reaction steps have conventionally been required.
- an object of the present invention is to provide an industrially advantageous process for producing cyclohexenone long-chain alcohol, which process requires a reduced number of reaction steps and can be performed with ease ' and at reduced production cost.
- the present inventors have performed extensive studies for developing a simple, convenient process for producing cyclohexenone long-chain alcohol starting from a known substance, and have found that when cyclohexenone of enol form which can be produced with ease from a known substance 1, 3-cyclohexanedione is subjected to Grignard reaction by use of ⁇ -halogeno long-chain alcohol whose hydroxyl group is protected through silylation, cyclohexenone long-chain alcohol can be obtained through a reduced number of steps, conveniently, at low production cost, and in an industrially advantageous manner, thus leading to completion of the invention.
- the present invention provides a process for producing cyclohexenone long-chain alcohol represented by the following formula (1) :
- R 1 , R 2 , and R 3 have the same meanings as above, and R 4 represents a C1-C5 alkyl group
- a Grignard's reagent prepared from C10-C18 ⁇ -halogenoalcohol whose hydroxyl group is protected through silylation, and hydrolyzing the resultant reaction product.
- each of R 1 , R 2 , and R 3 represents a hydrogen atom.
- at least one of these is methyl.
- R 4 represents a C1-C5 alkyl, with ethyl being particularly preferred.
- Examples of preferred starting compound (2) include 3- ethoxy-6-methyl-2-cyclohexen-l-one, 3-ethoxy-2, 6-dimethyl-2- cyclohexen-1-one, and 3-methoxy-2, 6, ⁇ -trimethyl-2-cyclohexen- 1-one.
- the starting compound (2) can be obtained through enolation and methylation of 1, 3-cyclohexanedione, which is available at low cost.
- the sequence in which enolation and methylation are carried out is not critical, and enolation may precede methylation or vice versa.
- R 1 , R 2 , and R 3 are hydrogen atoms, methylation is not necessary.
- Enolation may be performed by reacting 1,3- cyclohexanedione, which may optionally be methylated if necessary (e.g., 2-methyl-l, 3-cyclohexanedione) , with alcohol (R 4 OH) in the presence of an acid catalyst.
- the acid catalyst include p-toluenesulfonic acid and sulfuric acid.
- the reaction is carried out in a solvent such as toluene, xylene, methanol, or ethanol, at 60-150°C for 2 to 10 hours.
- Methylation is performed by, for example, reacting enolated 1, 3-cyclohexanedione, which may optionally be enolated if necessary, with a lithiation reagent such as lithium diisopropylamide obtained through reaction between alkyl lithium and diisopropylamine, then with a methylation agent such as methyl iodide.
- a lithiation reagent such as lithium diisopropylamide obtained through reaction between alkyl lithium and diisopropylamine
- the lithiation reaction is preferably performed by cooling a solution prepared by adding lithium diisopropylamine to tetrahydrofuran or hexane to -80 to 0°C (e.g., -78°C) , then adding optionally enolated 1,3- ' cyclohexanedione (preferably 3-ethoxy-2-cyclohexan-l-one) dissolved in tetrahydrofuran, hexane, etc.
- methylation is performed after adding methyl iodide to the resultant reaction mixture and heating the mixture to 5 to 30°C (e.g., room temperature), while stirring the mixture for 5 to 12 hours.
- the thus-obtained compound (2) is reacted with a Grignard's reagent prepared from C10-C18 ⁇ -halogenoalcanol whose hydroxy group is protected through silylation, and is then subjected to hydrolysis, to thereby produce a cyclohexenone long-chain alcohol (1) .
- a Grignard's reagent prepared from C10-C18 ⁇ -halogenoalcanol whose hydroxy group is protected through silylation, and is then subjected to hydrolysis, to thereby produce a cyclohexenone long-chain alcohol (1) .
- Examples of the C10- C18 ⁇ -halogenoalcanol which has undergone silylation include the compound represented by the following formula (3) :
- R 5 , R 6 , and R 7 represents a C1-C8 alkyl group)'.
- X include Cl, Br, and I, with Br being preferred.
- A include C10-C18 linear or branched alkylene or alkenylene groups, with C12-C16 linear or branched alkylene groups being more preferred, and C12-C16 linear alkylene groups being even more preferred, and tetradecylene and pentadecylene being most preferred.
- R 5 , R 6 , and R 7 include a methyl group, an ethyl group, an isopropyl group, and a t-butyl group.
- the Grignard's reagent used in the present invention can be obtained by a conventional method, through reaction between a silylated ⁇ -halogenoalcanol and magnesium.
- the reaction between the compound (2) and the Grignard's reagent is performed in the manner of an ordinary Grignard reaction, and preferably in an absolute solvent such as diethyl ether or tetrahydrofuran at 40-80°C for 0.5 to 3 hours .
- the subsequent hydrolysis is preferably performed in the presence of an acid such as p-toluenesulfonic acid, hydrochloric acid, or sulfuric acid.
- an acid such as p-toluenesulfonic acid, hydrochloric acid, or sulfuric acid.
- the resultant intermediate may be isolated and then forwarded to the next reaction step.
- the intermediate may be forwarded directly to the next reaction step, without being isolated.
- the intermediate or a target compound can be isolated from a reaction mixture through washing, extraction, recrystallization, chromatographic techniques, etc., solely or in combination.
- methyl iodide (1.21 mL, 19.45 mmol) was added thereto, and the temperature of the reaction mixture was allowed to rise to room temperature.
- the reaction mixture was stirred overnight, diluted with water (100 mL) , and then extracted three times with ethyl ether. The organic layers were combined, washed with an aqueous NaCl solution, dried over magnesium sulfate, filtered, and concentrated under reduced pressure.
- Hydrogen bromide 50 L was gradually added to a mixture of 1, 15-pentadecanediol (5.08 g, 20.8 mmol) and cyclohexane (50 mL) , and the resultant mixture was refluxed with heat for 6 hours, followed by separation into two layers, The aqueous layer was subjected to extraction with hexane three times. The organic layers were combined, washed with aqueous saturated sodium hydrogencarbonate solution and aqueous sodium chloride solution, dried over magnesium sulfate, and concentrated under reduced pressure.
- the mixture was stirred for one hour at room temperature.
- aqueous saturated ammonium chloride solution was added to the reaction mixture for separation into a methylene chloride layer (200 mL) and an aqueous layer (200 . mL) .
- the organic layer was dried over magnesium sulfate, filtered, and concentrated under reduced pressure.
- the reaction mixture was neutralized with sodium hydrogencarbonate, followed by extraction with ethyl ether three times.
- the organic layers were combined, washed with aqueous sodium chloride solution, dried over magnesium sulfate, filtered, and concentrated under reduced pressure.
- methyl iodide (0.77 mL, 12.4 mmol) was added, and the temperature of the reaction mixture was allowed to rise to room temperature. The reaction mixture was stirred for 18 hours at room temperature. Water (100 mL) was added thereto, and the resultant mixture was subjected to extraction three times with ethyl ether. The organic layers were combined, washed with an aqueous NaCl solution, dried over magnesium sulfate, filtered, and concentrated under reduced pressure.
- the process of the present invention for producing cyclohexenone long-chain alcohol involves a reduced number of reaction steps, can be performed with ease at reduced production cost, and thus finds utility in the industry.
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
Claims
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
PCT/JP2003/003994 WO2004087630A1 (en) | 2003-03-28 | 2003-03-28 | Process for producing cyclohexenone long-chain alcohols |
Publications (2)
Publication Number | Publication Date |
---|---|
EP1608612A1 true EP1608612A1 (en) | 2005-12-28 |
EP1608612B1 EP1608612B1 (en) | 2008-02-27 |
Family
ID=33105315
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP03715611A Expired - Lifetime EP1608612B1 (en) | 2003-03-28 | 2003-03-28 | Process for producing cyclohexenone long-chain alcohols |
Country Status (5)
Country | Link |
---|---|
US (1) | US7235700B2 (en) |
EP (1) | EP1608612B1 (en) |
CA (1) | CA2519178C (en) |
DE (1) | DE60319439T2 (en) |
WO (1) | WO2004087630A1 (en) |
Families Citing this family (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP3406586B1 (en) * | 2016-01-22 | 2020-12-30 | Taiho Pharmaceutical Co., Ltd. | Manufacturing method for high-purity cyclohexenone long-chain alcohol |
CN107032975B (en) * | 2016-02-03 | 2022-06-28 | 大鹏药品工业株式会社 | Preparation method of high-purity cyclohexenone long-chain alcohol |
Family Cites Families (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP1003706B1 (en) * | 1997-08-13 | 2003-03-05 | Meiji Milk Products Company Limited | Cyclohexenone long-chain alcohol and medicament containing same |
JP4469441B2 (en) | 1999-02-10 | 2010-05-26 | 明治乳業株式会社 | Preventive or therapeutic agents for neurodegenerative diseases |
JP4354585B2 (en) | 1999-09-22 | 2009-10-28 | 明治乳業株式会社 | Cyclohexenol derivatives and pharmaceuticals containing the same |
WO2002029014A2 (en) * | 2000-10-04 | 2002-04-11 | Meiji Dairies Corporation | Stem cell differentiation-inducing promoter |
JP4861560B2 (en) * | 2001-02-19 | 2012-01-25 | 株式会社明治 | Treatment for diabetic complications |
JP3836684B2 (en) * | 2001-02-19 | 2006-10-25 | 明治乳業株式会社 | Treatment for dysuria |
EP1392267A1 (en) | 2001-05-24 | 2004-03-03 | Meiji Dairies Corporation | Preventive or remedy for diseases caused by cerebrovascular disturbances |
CN1237065C (en) * | 2001-05-31 | 2006-01-18 | 香港中文大学 | Compsn of norcantharidin with anticancer drugs containing platinum and its usage |
JP4035332B2 (en) | 2002-01-22 | 2008-01-23 | 明治乳業株式会社 | Process for producing cyclohexenone long chain alcohols |
-
2003
- 2003-03-28 US US10/550,305 patent/US7235700B2/en not_active Expired - Lifetime
- 2003-03-28 DE DE60319439T patent/DE60319439T2/en not_active Expired - Lifetime
- 2003-03-28 CA CA002519178A patent/CA2519178C/en not_active Expired - Lifetime
- 2003-03-28 WO PCT/JP2003/003994 patent/WO2004087630A1/en active IP Right Grant
- 2003-03-28 EP EP03715611A patent/EP1608612B1/en not_active Expired - Lifetime
Non-Patent Citations (1)
Title |
---|
See references of WO2004087630A1 * |
Also Published As
Publication number | Publication date |
---|---|
DE60319439T2 (en) | 2008-06-19 |
CA2519178C (en) | 2010-01-12 |
DE60319439D1 (en) | 2008-04-10 |
EP1608612B1 (en) | 2008-02-27 |
CA2519178A1 (en) | 2004-10-14 |
US20060135818A1 (en) | 2006-06-22 |
WO2004087630A1 (en) | 2004-10-14 |
US7235700B2 (en) | 2007-06-26 |
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Inventor name: SUZUKI, HIROTO,MEIJI DAIRIES CORPORATION Inventor name: YAMADA, MASASHI,MEIJI DAIRIES CORPORATION Inventor name: TRANCARD, DELPHINE,CNRS, UNIVERSITE LOUIS PASTEUR Inventor name: OHSHIBA, YUKIO,MEIJI DAIRIES CORPORATION Inventor name: NEUBERG, PATRICK,CNRS, UNIVERSITE LOUIS PASTEUR Inventor name: LUU, BANG,CNRS, UNIVERSITE LOUIS PASTEUR |
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